Luteolin 7-rutinoside

Food Chem. 2012 Nov 15;135(2):764-9.

Isolation of some luteolin derivatives from Mentha longifolia (L.) Hudson subsp. longifolia and determination of their genotoxic potencies.[Pubmed: 22868156 ]

This study was designed to evaluate the mutagenic and antimutagenic activities of luteolin derivatives (luteolin 7-O-glucoside, luteolin 7-O-rutinoside and luteolin 7-O-glucuronide) isolated from Mentha longifolia (L.) Huds. subsp. longifolia by using Ames Salmonella test (TA 1535 and TA1537 strains).
METHODS AND RESULTS:
In the antimutagenicity assays, luteolin 7-O-glucoside, luteolin 7-O-rutinoside(Luteolin 7-rutinoside) and luteolin 7-O-glucuronide showed antimutagenic effects on TA1537 and TA1535 strains. The highest inhibition rates for luteolin 7-O-glucoside, luteolin 7-O-rutinoside and luteolin 7-O-glucuronide on TA1537 strain were 84.03%, 87.63% and 67.77%, respectively. Similarly, in the antimutagenicity assays performed with the TA1535 strain, the inhibition rates for luteolin 7-O-glucoside and luteolin 7-O-rutinoside(Luteolin 7-rutinoside) were 23.86% and 23.76% respectively.
CONCLUSIONS:
Our findings showed that the antimutagenic properties of luteolin derivatives on TA1537 and TA1535 strains have been found to be structure dependent. The clarification of differences in antimutagenic potency of these luteolin derivatives based on their structures has been demonstrated in this study.

J Agric Food Chem. 2004 Dec 1;52(24):7272-8.

Phenolic compounds from the leaf extract of artichoke (Cynara scolymus L.) and their antimicrobial activities.[Pubmed: 15563206 ]

METHODS AND RESULTS:
A preliminary antimicrobial disk assay of chloroform, ethyl acetate, and n-butanol extracts of artichoke (Cynara scolymus L.) leaf extracts showed that the n-butanol fraction exhibited the most significant antimicrobial activities against seven bacteria species, four yeasts, and four molds. Eight phenolic compounds were isolated from the n-butanol soluble fraction of artichoke leaf extracts. On the basis of high-performance liquid chromatography/electrospray ionization mass spectrometry, tandem mass spectrometry, and nuclear magnetic resonance techniques, the structures of the isolated compounds were determined as the four caffeoylquinic acid derivatives, chlorogenic acid (1), cynarin (2), 3,5-di-O-caffeoylquinic acid (3), and 4,5-di-O-caffeoylquinic acid (4), and the four flavonoids, Luteolin 7-rutinoside (5), cynaroside (6), apigenin-7-rutinoside (7), and apigenin-7-O-beta-D-glucopyranoside (8), respectively.
CONCLUSIONS:
The isolated compounds were examined for their antimicrobial activities on the above microorganisms, indicating that all eight phenolic compounds showed activity against most of the tested organisms. Among them, chlorogenic acid, cynarin, luteolin-7-rutinoside, and cynaroside exhibited a relatively higher activity than other compounds; in addition, they were more effective against fungi than bacteria. The minimum inhibitory concentrations of these compounds were between 50 and 200 microg/mL.

Molecules. 2009 Jan 22;14(1):509-18.

Antimutagenic activity and radical scavenging activity of water infusions and phenolics from ligustrum plants leaves.[Pubmed: 19169198 ]

Water infusions of Ligustrum delavayanum and Ligustrum vulgare leaves and eight phenolics isolated therefrom have been assayed in vitro on ofloxacin-induced genotoxicity in the unicellular flagellate Euglena gracilis.
METHODS AND RESULTS:
The tested compounds luteolin, quercetin, luteolin-7-glucoside, Luteolin 7-rutinoside, quercetin-3-rutinoside, apigenin-7-rutinoside, tyrosol and esculetin inhibited the mutagenic activity of ofloxacin (43 microM) in E. gracilis. Water infusions from leaves of L. delavayanum and L. vulgare showed higher antimutagenic effect (p(t) < 0.001). The activity of these samples against ofloxacin (86 microM)-induced genotoxicity was lower, but statistically significant (p(t) < 0.05), excluding the water infusion of L. delavayanum leaves (p(t) < 0.01). Efficacy of quercetin, luteolin-7-rutinoside, apigenin-7-rutinoside was insignificant.
CONCLUSIONS:
The antimutagenic effect of most phenolics we studied could be clearly ascribed to their DPPH scavenging activity, substitution patterns and lipophilicity.

Biol Pharm Bull. 2002 Feb;25(2):256-9.

Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L.[Pubmed: 11853178 ]

METHODS AND RESULTS:
Six flavonoid glycosides, eriocitrin (1), narirutin (2), hesperidin (3), luteolin-7-O-rutinoside (Luteolin 7-rutinoside,4), isorhoifolin (5), diosmin (6), rosmarinic acid (7) and 5,7-dihydroxycromone-7-O-rutinoside (8), were isolated from the aerial part of Mentha piperita L. Among these compounds, compound 4 showed a potent inhibitory effect on histamine release induced by compound 48/80 and antigen-antibody reaction. This compound was more effective than luteolin and luteolin-7-O-glucoside in inhibiting histamine release from rat peritoneal mast cells. Compound 4 also caused a dose-related inhibition of the antigen-induced nasal response and significant effects were observed at doses of 100 and 300 mg/kg.
CONCLUSIONS:
These results indicate that compound 4 may be clinically useful in alleviating the nasal symptoms of allergic rhinitis.

Food Chem Toxicol. 2011 Feb;49(2):376-84.

Extraction and identification of three major aldose reductase inhibitors from Artemisia montana.[Pubmed: 21092751 ]

Aldose reductase inhibitors (ARIs) provide an important therapeutic and preventive opportunity against hyperglycemia associated diabetic complications.
METHODS AND RESULTS:
The methanolic extracts of 12 species from the genus Artemisia exhibited significant in vitro rat lens AR (RLAR) inhibitory activities with IC(50) values ranging from 0.51 to 13.45 μg/mL (quercetin, 0.64 μg/mL). Since the whole plant of Artemisia montana showed the highest RLAR inhibitory activity, bioassay-guided fractionation was performed to obtain ethyl acetate and n-butanol fractions. Repeated column chromatography of two active fractions, yielded fifteen compounds, including four chlorogenic acids (3,5-di-O-caffeoylquinic acid, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid), six flavonoids (apigenin, luteolin, quercetin, isoquercitrin, hyperoside, Luteolin 7-rutinoside), and five coumarins (umbelliferone, scoparone, scopoletin, esculetin, and scopolin); their structures were confirmed by spectroscopic methods. 3,5-Di-O-caffeoylquinic acid and chlorogenic acid, as well as test flavonoids, displayed the most potent RLAR inhibitory activities with IC(50) values ranging from 0.19 to 5.37 μM. Furthermore, the HPLC profiles of the ethyl acetate and n-butanol fractions indicated that 3,5-di-O-caffeoylquinic acid, chlorogenic acid, and hyperoside, as major compounds, might play crucial roles in RLAR inhibition.
CONCLUSIONS:
The results suggest that A. montana and three key AR inhibitors therein would clearly be potential candidates as therapeutic or preventive agents for diabetic complications.